Simon Cecil sat on a metal stoop at the Hennepin County jail's exit, studying a mug shot of a man he's never met but just paid $50 to bail out.

Mug shots rarely capture a flattering likeness, and Cecil has learned that calculating the time it takes to discharge someone from jail is a science of educated guessing, so he stares at every face moving to the door, looking for David Stribling. After about half an hour, Cecil spots a guy who might be Stribling, but when he approaches, the stranger shakes his head and asks for a cigarette.

Another hour creeps by and a goateed man emerges wearing a brown flannel shirt and carrying a paper bag. This looks even more like Cecil's man, but he's wearing a dark hat that makes it hard to say for sure.

"Mr. Stribling?" Cecil asks. The man nods in the affirmative, and Cecil tells him he's the one who posted his bail.

"Why did you do that?" Stribling asks cheerfully, an unlit cigarette hanging from his lips.

Cecil has this part down to a tight 30 seconds: I work for a nonprofit called the Minnesota Freedom Fund. We post small-amount bails for people who can't afford to. All we ask is that you show up for your next court date.

"I'll definitely show up to court," Stribling promises of his citation for violating a no-contact order. He studies the business card he's just been handed. "Simon Cecil," he reads aloud. "It sounds like a senator name."

Cecil is not a senator, but a 34-year-old University of Minnesota student readying to graduate with dual master's degrees in business and public policy. Cecil started the Freedom Fund last fall, a so-called "bail fund" that mirrors similar efforts in places like New York City and Chicago.

If someone is held on a bond under $1,000 and doesn't have the resources to post, Cecil will bail him or her out. As long as the defendant shows up for court, the money goes back to the fund. So far, all but two have made good on that promise.

The success of the fund is already gaining traction with others in the criminal justice system. A group that includes Hennepin County judges, defense attorneys and community organizers has been meeting since November with the goal of starting a larger-scale fund that could expand to more people and more counties.

Yet their endeavor goes beyond just posting bond. The group believes Minnesota's bail system is fundamentally broken. And to truly solve that, they acknowledge, is going to be much trickier.

The evolution of bail

Contrary to the conventional wisdom of prime-time television dramas, the American bail system was not invented as a means of criminal punishment. Rather, bail is a contract designed to incentivize people to return to court after being accused of a crime, when they are still presumed innocent.

When someone is arrested, the court assesses the person's risk of not returning. The judge also weighs the potential threat to public safety. In rare circumstances the person must remain in jail until the outcome of the case. In other cases, a judge will determine a defendant poses such little flight risk or community threat, the person can simply go free on their promise to return.

The third option is that the court will conditionally release the individual. If the condition is money, this is called a "bond." As the bail system has transmutated over the centuries, this is where reformers say it has gone very wrong.

The Eighth Amendment to the United States Constitution prohibits "excessive" bail. Yet 34 percent of Americans charged with crimes linger in jail pretrial for no other reason than they can't afford to pay, according to a 2016 report by the Harvard Law School. Most of these people come from poverty. In Hennepin County, defendants regularly sit in jail on low-cash bails they can't afford.

"I've even seen some $10 bails," said Hennepin County Judge Bridget Sullivan. "And people are just sitting in jail because they can't make this really low bail."

Making bail can be the difference between guilty or innocent. The Harvard study cited that defendants stuck in jail were 25 percent more likely to plead guilty than someone who's been released.

"It isn't fair that simply because a person can post bail they're going to get a different resolution than a person who has to stay in jail," said Chief Hennepin County Public Defender Mary Moriarty. "What that means is that people who can afford it get better justice than poor people."

This disproportionate impact on the poor is the core driver in a wave of bail reform happening in America. New Jersey is the latest state to upend its bail system, implementing a nuanced screening process this year that reshuffles bond as a last resort.

Minnesota has so far been quiet in this national conversation. But behind the scenes, efforts like Cecil's Freedom Fund are driving toward changing the system.

The Freedom Fund is one of about 10 such bail funds in the country, said Cherise Fanno Burdeen, executive director of Maryland-based Pretrial Justice Institute.

Burdeen calls these funds a manifestation of frustration with bail — a workaround of the system rather than a cure. But as reforms continue to take hold around the nation, Burdeen said, bigger changes may be on the horizon.

"By the end of this year we'll be at a tipping point where there's no going back," she said.

The business of bail

Cecil now spends long days and nights waiting in the jail lobby to bail people out. But he once found himself on the other side of this equation.

In 2008, he'd been certified as an EMT, and attended the Republican National Convention to provide medical aid to demonstrators. Police picked him up in a mass arrest and he spent two days in the Ramsey County jail before a friend bailed him out for $200. Prosecutors ultimately dropped the unlawful assembly charge, and Cecil and others unsuccessfully sued the city for the arrest.

Cecil's experience as a social activist helped shape his belief that something was systematically failing in Minnesota's criminal justice system. About a year ago, with the help of his classmate, Adam Rao, Cecil pitched the idea for a bail fund to a program through the University of Minnesota's Carlson School of Management, which gives seed money to students with innovative start-up proposals. The school awarded him $5,000, and he won another $5,000 through a business competition called the "Acara Challenge," which also helps fund creative projects with real-world potential.

With $10,000 in the bank, Minnesota Freedom Fund was in business.

For clients, Cecil turned to defense attorneys, and he's set up a deal in which public defenders send him names of defendants who are stuck in jail with small-amount bails.

Cecil quickly learned that posting bond can be more complicated than simply paying the fee. He usually arrives to the jail at night, and sits in the lobby for up to five hours waiting for the person to be released. He never knows whom he's bailing out, so he buys a $1 mug shot when he arrives. Sometimes the person has outstanding warrants or probation issues, which can delay the process. Bail also requires exact change — cash only — and bailiffs frequently send him to make change at the nearby light rail pay station.

Cecil said he's been frustrated to see bails that don't appear to relate to motivating the person to return to court or public safety. He frequently sees bail set at $78, the exact amount of the surcharge for court fees in Hennepin County.

"That's not about likelihood to return, that's not about threat to the community," he said.

Though Moriarty casts the bail fund as merely a "Band-Aid," she said the fund is already making a difference. She said clients who can't afford bail often take deals offered by prosecutors where they agree to plead guilty for a penalty of "time served" — meaning the time they've already spent in jail — instead of trying to fight it. This gets them out of jail, but creates a criminal record that could come back to haunt them.

The bail fund has allowed defendants options, Moriarty said. In one instance, prosecutors dropped charges before a case went to trial. In another, a client suffering from a mental breakdown was able to get psychological help — admitted to the Hennepin County Medical Center's Acute Psychological Unit for a 72-hour lockdown — instead of languishing in jail, where her mental condition may not have been properly treated. One person was able get out of jail and show up for work, and otherwise may have lost his job.

When Cecil first launched the fund, he set out to post bail for at least 10 people, he said. But "once we hit 10 and it was working we just kept going."

As of publication, he's bailed out 33 people.

Building better bail

Judge Sullivan witnessed bail system's disproportionate impact on low-income people in her first year on the bench. As a new judge, the court assigned her to the misdemeanor calendar, where she presided daily over a revolving line of low-level crime cases.

"Oh my God," she remembers thinking. "There are people here with $50 bail and they can't post. And they're just sitting in jail."

Sullivan had read about bail funds in other major cities, and wondered if something like it existed in Minneapolis. Last fall, she and another judge contacted Michael Friedman, director of Legal Rights Center, a nonprofit, advocacy-driven law firm that works as an alternative to the public defender system.

Since November, Sullivan, Friedman and a group of others have been meeting at the Legal Rights Center trying to figure out how to build on Cecil's idea. They hope to file for nonprofit status this year, and they're talking to donors about securing more funding. Friedman said it's still too early to say what will come of this, but they hope to create a deeper fund that could reach more low-income people in jail, possibly widening the scope to other county jails in the Twin Cities.

But the fund is just the first step — not the end game, said Friedman. "[We're] creating an organization that wants to be out of business," said Friedman. "We're working on this bail fund, but the goal is: the entire conception of money bail is flawed."

Andy Mannix • 612-673-4036